Results tagged ‘ Theo Epstein ’

Cubs, Epstein agree on five-year contract extension

theo(Photo by Sean M. Haffey/Getty)

Chicago Cubs Chairman Tom Ricketts announced that the team and President of Baseball Operations Theo Epstein have agreed to terms on a five-year contract extension.

“In the five years under Theo’s leadership, he has brought in a strong executive team and acquired and developed some of the best players in the game. Now, the results are on the field. My family and I have no doubt that we have moved closer to our goal of delivering Cubs fans the World Series Championship they deserve,” Ricketts said, adding that the contract “ensures the baseball operations team assembled by Epstein will continue its remarkable tenure of building a consistent championship contender.”

“Both on the baseball and business sides, I believe we have the best leadership in the league and we are well positioned for sustained success,” Ricketts said.

Epstein originally joined the Cubs on Oct. 25, 2011, under the terms of a five-year deal. The major-league club has progressed from a 61-101 record in 2012 to 101 wins with five games remaining just four years later, becoming just the third team in major-league history to win at least 100 games within four years of a 100-loss season. Since 2012, the organization progressed to a 66-96 record in 2013 and a 73-89 mark in 2014 before surging to a 97-65 mark in 2015, the third-best record in all of baseball and an eventual spot in the National League Championship Series.

The 2016 Cubs clinched the best record in all of baseball with more than a week remaining in the regular season, reaching 100 wins for the first time since 1935 and maintaining the possibility of posting one of the top three win totals in 140 years of Cubs baseball. The Cubs have qualified for postseason play in consecutive seasons for only the third time in their modern baseball history.

During his time with the Cubs, Epstein has expanded both the size and scope of baseball operations leadership, increasing the organization’s emphasis in amateur, professional and international scouting, player development, analytics, research and development, medical operations and beyond.

Since taking over baseball operations, Epstein and his group have rebuilt the organization by making more than 40 trades to acquire players such as Anthony Rizzo, Jake Arrieta, Addison Russell, Dexter Fowler and Kyle Hendricks; have been aggressive on the free-agent market to sign players such as Jon Lester, Jason Heyward, Ben Zobrist and John Lackey; selected impact talent such as Kris Bryant, Kyle Schwarber and Albert Almora Jr. in the amateur draft; selected Hector Rondon in the Rule 5 Draft; signed Jorge Soler and many other future Cubs in the international market; and hired 2015 NL Manager of the Year Joe Maddon.

Epstein joined the Cubs after 10 seasons with the Boston Red Sox, the last nine as the club’s General Manager. He built World Champion ballclubs in 2004 and 2007, winning the organization’s first World Series title in 86 years, and saw four teams advance to the American League Championship Series (2003, 2004, 2007, 2008).

2016 Cubs Convention: Baseball Management

After the highly successful 2015 season, the Baseball Operations department has been hard at work gearing up for the 2016 campaign. Len Kasper interviews President of Baseball Operations Theo Epstein, Executive Vice President/General Manager Jed Hoyer, and Assistant General Managers Randy Bush and Shiraz Rehman about the offseason and what lies ahead in 2016.

Theo Epstein opened up the panel, thanking fans for their loud applause during the Opening Ceremony. He discussed the successful offseason, especially with Jason Heyward, where he felt it didn’t feel like signing a free agent, it felt more like adding to our young core. Adam Warren, the return for Starlin Castro, is a guy that could sneak up on people.

Hoyer was reminded of how hard it wins 97 games. He and Epstein looked at each other that last week as the wins kept racking up, and were in some disbelief.

They were asked at what point they may part with members of the elite bench or prospects for top-level players, and they said that with so much talent on the major league front, they may be more willing to dip into the minor league depth.

The front office is extremely excited about Minor League Player of the Year Willson Contreras, and they see him as an incredibly talented catcher. He projects to be a front-line backstop in the big leagues for a long time.

They were asked about some drastic splits with a few of the young Cubs, and how they can be better balanced. Hoyer think Kyle Schwarber will be able to hit lefties if they allow him enough at-bats, which they plan to do. He believes Kris Bryant’s home/road splits are a little more random. They also just hope Jorge Soler will get used to the cold weather.

Hundley discussed the difference of Wrigley Field versus any other stadium in terms of hitting. He says the weather plays a big role and there is an adjustment period involved, especially with young players.

Rehman was asked about the back-to-back transaction of the Ben Zobrist signing turning into a Starlin Castro-for-Adam Warren deal. He said a lot of work is involved.

“Getting access to starting pitching was something we really wanted to do this winter,” Rehman reiterated.

Epstein also brought up that relationships and trust are important when making multi-level moves. He said it took almost two full months of Zobrist’s trust. They also had talked about the Castro-for-Warren deal with the Yankees at the 2015 trade deadline.

Hoyer anticipates the changes of the international market spending policies. There could be an international draft at some point soon.

Epstein said they have so many hitters coming up, that they all would like a designated hitter, but it’s out of their hands.

With regards to adding talent prior to Spring Training, Hoyer talks every day with teams and agents trying to upgrade the team. But they’re not looking for big changes at this point. There is a lot of versatility, both with the position players and the pitchers. He believes the Cardinals are going to be good year after year, but it’s in the Cubs’ best interest to build the best roster for themselves.

Epstein is planning for projected lineups for the next half decade. He made that point to state they won’t abandon the search for young players and hope to keep a deep farm system.

Epstein said there was plenty of talent ready for him in Boston that they were able to win from the beginning. He realized when he got to Chicago, he needed to build from the ground up. He thanked fans for their patience and he hopes the upcoming seasons will be worth it.

Rehman thinks the players enjoy the idea of potentially coming in and playing positions or doing something they maybe haven’t done in previous seasons. It makes it fun for the front office too because manager Joe Maddon is willing to try something new or outside of the box when a transaction is proposed.

Epstein isn’t a fan of the arbitration. He hasn’t had a player go to arbitration in 15 years. They are the biggest Jake Arrieta fans and they want to see him in a Cubs uniform for the foreseeable future.

The Cubs were aggressive this offseason because of how “dry” the upcoming free-agent class is going to be. They don’t want to rely on free agency every year.

When going into a draft, the front office talks about the person drafted just as much as the player. They are going to have to project how a young player gets challenged in a new situation.

From the Pages of Vine Line: Joe Maddon’s relationship with the front office is built to last


Photo by Stephen Green

Joe Maddon and his players are clicking as the Cubs have won 10 of their last 11 games. Part of the reason for that success is that Maddon and the front office have been on the same page since he was hired in November. The following can be found in the August issue of Vine Line.

Too often, the marriage between field manager and front office goes from bliss to blisters before the honeymoon cruise returns to port. With both sides intent on stressing their points, everyone stresses out, creating irreconcilable differences not even a championship can cure.

But you don’t need a marriage counselor to certify the relationship between first-year Cubs skipper Joe Maddon and his bosses, President of Baseball Operations Theo Epstein and Executive Vice President and General Manager Jed Hoyer, is built to last.

“We all understand no one person has all the answers,” Maddon said. “The most important thing is that nobody has to be right. It’s just about getting it right.”

Epstein and Hoyer, both 40 when they hired Maddon last fall, felt secure enough to bring in a manager 20 years their senior. And Maddon, who was 60 at the time, welcomed the opportunity to work with and learn from aggressive, young leaders, as he had in Tampa Bay with Andrew Friedman.

“They’re all way beyond me when it comes to [intellect],” said the typically self-deprecating Maddon. “But I really like being pushed and expanded.”

The Cubs skipper may know what to say, but a yes-man he is not.

Consider the Spring Training dialogue over the future of 22-year-old prospect Javier Baez. Maddon felt the struggling young hitter could continue to develop in the major leagues under the tutelage of the Cubs coaching staff. Epstein and Hoyer advocated more Triple-A seasoning. The latter view ultimately prevailed, but the two sides moved on together as a unified front.

“Our talks are always wide open,” Maddon said. “No one is worried about someone else’s feelings. Nobody worries about whose idea something is.”

Such is the case when mutual respect reigns. Maddon signed on knowing Epstein and Hoyer captured World Series titles with Boston in 2004 and 2007. For his part, Maddon managed low-budget Tampa Bay to four playoff berths in nine years, including a losing World Series appearance against Philadelphia in 2008. In that season’s ALCS against Boston, Maddon left tire tracks on Epstein and Hoyer as his resilient Rays eliminated the BoSox in seven games.

Before the 2004 season, the front-office pair nearly hired Maddon—then Mike Scioscia’s bench coach with the Angels—to manage their Boston squad. Instead, they tapped Terry Francona, and Maddon didn’t get his managerial shot until 2006 with Tampa Bay.

Still, Epstein and Hoyer never lost sight of the man with the black horn-rimmed glasses. When a contractual exit clause made Maddon a free agent last fall, the astute Cubs executives snatched him up.

Maddon’s passion for helping develop talent is well documented, but he also thrives on partnering with young, modern-thinking executives. Former Rays GM Friedman was just two days past his 29th birthday when he gave himself a present and hired Maddon to manage a team that had averaged 97 losses in its first eight years of existence.

Maddon recognizes in Epstein and Hoyer the same qualities he appreciated in Friedman.

“These guys are cut from the same intellectual cloth,” Maddon said. “Conversations with them cover everything. I might be way out here on a subject, and they bring me back with a thought I hadn’t even considered yet. And sometimes I do the same for them. We have a common goal.”

Epstein and Hoyer, after employing two less-accomplished field generals in their first three Cubs seasons, appreciate Maddon all the more. Secure in his leadership skills, they’re free to tackle issues like player procurement and international markets while leaving day-to-day communications with players and the media to the manager. Moreover, they no longer feel obliged to micromanage the use of young pitchers as a means of protecting their assets.

“Their questions are really good, and I enjoy well-thought-out questions,” Maddon said. “But they do respect what I’ve done in the past, and that includes, to a large extent, the developing of young players.”

Epstein praises Maddon’s ability to meld talent of varying backgrounds and experience. As for bedside manner, even the manager’s toughest messages are delivered with positive prefaces and epilogues.

“We’ve made the usual young mistakes and mental mistakes all developing clubs make,” Epstein said. “It’s a credit to Joe and his staff that it’s usually cleaned up within a day. He doesn’t get bogged down in mistakes or let them bother him or the atmosphere around the club.”

Suffice it to say Cubs management trusts Maddon with the organization’s crown jewels.

“Any time you can improve from within, it’s the most efficient way to get better,” Epstein said. “Joe and his staff help our players relax and get better. When we bring in a player, we know he’ll be attended to in the proper way. We’re thrilled with the way players have grown, and the identity of the team has been an obvious strength.

“We haven’t accomplished anything yet, but that doesn’t mean we aren’t proud of the team and having a lot of fun.”

May the honeymoon never end.

—By Bruce Levine and Joel Bierig

Eddie Vedder joins the Hot Stove Cool Music concert lineup

Vedder140724_Cubs_021Pearl Jam frontman and rock icon Eddie Vedder will take the stage at the fourth annual Hot Stove Cool Music Chicago benefit concert on July 9 at Wrigleyville’s Metro. Vedder will join Chicago Cubs President of Baseball Operations Theo Epstein, Hall of Fame baseball writer Peter Gammons and Chicago Cubs broadcaster Len Kasper as part of the all-star music lineup at the annual event celebrating music, baseball and charitable giving.

“We are thrilled and honored Eddie Vedder has volunteered to play the show and help raise money for deserving nonprofits in Chicago,” said Chicago Cubs President of Baseball Operations and Foundation To Be Named Later co-founder Theo Epstein. “Hot Stove Cool Music revolves around the power of music, baseball and community involvement. There’s no better person to represent that spirit than Eddie. He’s a rock legend, a tried-and-true Cubs fan and he has a tremendous heart. It will be a memorable night for everyone.”

The fundraiser will feature ensemble performances by Chicago and Boston rockers including John Stirratt (Wilco), Daxx Nielsen (Cheap Trick), Jennifer Hall, Matt Spiegel and Curt Morrison (Tributosaurus), Freda Love Smith (Blake Babies, Mysteries of Life), Jake Smith (Mysteries of Life), Gerald Dowd, Jason Narducy (Split Single, Bob Mould), Brendan Bayliss (Umphrey’s McGee), Will Dailey, Chris Cote, Phil Aiken, Paul Ahlstrand and more. WXRT’s Lin Brehmer, actor Joel Murray and actor/comedian Mike O’Malley will serve as the evening’s emcees.

A limited amount of general admission tickets will be released today at noon. Tickets will be available for $75 online at or in person at the Metro box office located at 3730 N. Clark St. There will be no service fees for cash purchases at the Metro box office. VIP tickets can also be purchased online at

Proceeds benefit Cubs Charities and Epstein’s Foundation To Be Named Later (FTBNL). Both nonprofit organizations share the same mission to help underserved youth in Chicago.

Theo Epstein’s Hot Stove Cool Music guest list announced

Music and baseball will be in the same lineup again at Wrigleyville’s Metro on July 9, when Chicago Cubs President of Baseball Operations Theo Epstein, Hall of Fame baseball writer Peter Gammons and Cubs broadcaster Len Kasper join an all-star lineup of musicians and personalities for the fourth annual Hot Stove Cool Music Chicago benefit concert. The annual event celebrates music, baseball and giving back.

Benefiting Epstein’s Foundation To Be Named Later (FTBNL), the fundraiser will feature ensemble performances by a special guest “headliner to be named later” (at the headliner’s request) and noted rockers from Chicago and Boston. The lineup includes Jimmy Chamberlin (Smashing Pumpkins), John Stirratt (Wilco), Daxx Nielsen (Cheap Trick), Jennifer Hall, Matt Spiegel and Curt Morrison (Tributosaurus), Freda Love Smith (Blake Babies, Mysteries of Life), Jake Smith (Mysteries of Life), Gerald Dowd, Jason Narducy (Split Single, Bob Mould) and more. Epstein, Gammons and Kasper also will perform with the bands. WXRT’s Lin Brehmer, actor Joel Murray and actor/comedian Mike O’Malley will serve as the evening’s emcees.

“The foundation is grateful for the incredible generosity of the musicians, sponsors and fans who dedicate their time, effort, energy and, most importantly, their passion to help us provide opportunities for Chicago youth by supporting the organizations that work tirelessly as their advocates,” said FTBNL co-founder Theo Epstein. “We’ve collectively raised more than $6 million and look forward to increasing that total this year through another great night of music, baseball and giving back.”

Tickets go on sale on Friday, May 22, at noon CST. General admission tickets are $75, and there will be no service fees for cash purchases. Fans can buy tickets online at or in person at the Metro Box Office located at 3730 N. Clark St. VIP tickets also will be available at

In addition to the all-star music lineup, the evening will include several special guests as well as live and silent auctions featuring signed sports memorabilia and priceless entertainment experiences.

Nonprofit beneficiaries include Chicago Children’s Choir, Chicago Wapiti RFC, City Year Chicago, Family Reach Foundation, Garfield Park Little League, Girls in the Game, Jackie Robinson West, Marwen, Special Olympics and South Chicago Arts Center.

For more information on Foundation To Be Named Later programs and events, or to make a donation, please visit

Now Playing: A memorable Opening Night at Wrigley Field

There’s nothing like Opening Day (or Night) to get you excited for the season. The North Siders are coming off a huge offseason, and this was many fans’ first opportunity to see new manager Joe Maddon, prized free-agent lefty Jon Lester, leadoff hitter Dexter Fowler and the rest of the team in person. Plus, the Cubs were the nationally televised, ESPN2 Opening Night affair—the only game on the major league slate—and debuted the new 3,990-square-foot video board in left field. To make things even better, the Cardinals were in town, and it was Lester toeing the slab versus St. Louis ace Adam Wainwright. The house was packed, and it felt like a playoff atmosphere. If you couldn’t be at Wrigley Field Sunday night, Vine Line was there to give you a look at all the Opening Night festivities.

ESPN’s Law ranks the Cubs’ system best in baseball


Kris Bryant heads what Keith Law calls the best system in baseball. (Photo courtesy of Getty Images)

In July, ESPN prospect expert Keith Law raved about the Cubs’ system, naming it the best in the game at that point. He went so far as to say, “This has to be the most loaded the Cubs’ farm has been in at least 30 years.”

That feeling has continued to resonate with Law, who again named the Cubs’ farm system the best in baseball heading into the 2015 season.

1. Chicago Cubs

The Cubs’ draft strategy under the Theo Epstein/Jed Hoyer regime has been to grab a polished hitter in the first round and load up on arms later. That, along with the trade of Jeff Samardzija and Jason Hammel that netted two more top hitting prospects, has produced a system that’s full of hitting prospects but still a bit light on the pitching side. The first wave of bats reached the majors in the middle of 2014, with more coming this year, but there won’t be enough at-bats for Javier Baez and Jorge Soler and Arismendy Alcantara and Addison Russell and Kyle Schwarber and Starlin Castro and Anthony Rizzo … and that’s not even everyone who might end up pushing for playing time. The Cubs are in prime position to flip a young hitter for a pitcher or even to swing a bigger deal, especially if they want to try to set themselves up to win the NL Central in 2016. There are young starting pitching prospects here to like, led by 20-year-old Duane Underwood, but they’re all a few years away.

Law ranked the Cubs the No. 4 system at this time in 2014, No. 5 in 2013, and No. 20 in 2012—mere months after Epstein and Hoyer took over.

Law will unveil his top 100 prospects on Thursday and list his top 10 prospects for each club on Friday.


2015 Cubs Convention: Meet Cubs Baseball Management

Through a series of trades, free agent signings and the hiring of new manager Joe Maddon, this offseason has been busy for the Baseball Operations department. On Saturday morning, Cubs radio broadcaster Ron Coomer and CBS Radio personality Josh Liss met with President of Baseball Operations Theo Epstein, Executive Vice President/General Manager Jed Hoyer, Assistant General Manager Randy Bush and Assistant General Manager Shiraz Rehman to discuss how the offseason unfolded. Here’s what went down with the Baseball Operations department at the 2015 Cubs Convention:

Josh Liss kicks things off thanks to the new CBS partnership. Coomer talks about having total knee replacement surgery in the offseason. He looks pretty good for eight weeks out from surgery. Coomer opens by talking about the excitement of the Cubs this season. “Baseball is a better game when the Cubs are good,” Coomer says.

When asked about the team’s confidence, Epstein mentions that the team is still undefeated in 2015. He’s done tempering expectations. Cubs fans deserve to get excited after the last three years. He thinks the team will be really fun to watch this year.

“When you have players who have won the World Series and been to the top of the mountain, it provides great perspective for everyone else.,” Epstein says of signing Jon Lester. Bush talks about how experienced players can be steadying for the club.

Bush and Rehman talk about working for Epstein and Hoyer.

“It’s a pretty dynamic place to go to work every day,” Bush says. “It’s a pretty exciting group of guys from Theo all the way down. … It’s one of the most exciting places I’ve ever come to work.”

Rehman talks about the strides the team has made rebuilding the farm system. The trades they made were tough, but they were building for the future. Now that’s starting to pay off.

Bush talks about Epstein/Hoyer’s great sense of humor and how smart they are. They’re all about gathering information and accumulating as many resources as possible about players.

Hoyer and Epstein talk about their trip to a Florida RV park to land Maddon. They knew it was a great opportunity and wanted to be aggressive. Maddon was traveling the county in his RV (the Cousin Eddie). They met him in Florida and realized they hadn’t brought anything for Maddon and his wife. They quickly made a stop at Publix to get some wine. They sat and talked baseball for about six hours on plastic chairs in the sand. Epstein talks about how engaging Maddon is and how he can bring out the best in you. Players feel that too. Two days later, they were in Maddon’s agent’s office in Chicago hammering out a contract.

“When things present themselves that are such great opportunities, don’t overthink things. Just pounce,” Epstein says of Maddon’s hiring. Says he’s missed out on other opportunities/players by not being so aggressive. You deal with the ramifications later.

Hoyer talks about the challenges of playing/managing in Chicago, but says Maddon is great at finding creative solutions to bringing teams together. Won with few resources in Tampa.

Maddon understands that players need to have a life away from the ballpark, Hoyer says. You need to keep players fresh and keep things interesting. He has days when players don’t have to show up early for batting practice, themed trips, etc.

Hoyer talks about the new coaches. Calls Dave Martinez a future manager. Talks about Mallee’s work in Houston with guys like Jose Altuve and Cris Carter. Plus, he has had success with right-handed power hitters (which the Cubs have a lot of).

Epstein says Eric Hinske will be a nice complement to Mallee as asst. hitting coach. Very different personalities. Also talks about the guys who are coming back, Borzello, Strode, Jones, Bosio, etc.

Borzello and Bosio work amazingly hard breaking down hitters and going over scouting reports. Epstein says every time he goes into coaching room, those guys are watching video, breaking down opposing hitters. Rehman says he and Borzello had an hour-long conversation last night after midnight about pitch-framing. That’s the kind of passion these guys have for the game, he says.

Now we’re on Jon Lester. Epstein talks about how Lester could have gone a lot of places given his career, character, track-record, but he was up for the challenge of coming to Chicago. At dinner after the initial meeting, Lester kept saying, “They’re going to burn this city down again when we win the World Series.”

They really tailored the pitch to Lester because they knew him. Felt like they were cheating because they knew so much about Lester and his family. But, ultimately, Lester simply wanted to come here.

Epstein talks about Lester’s pitch mix and his experience pitching at Fenway. It has forced him to get creative and be adaptable. He should be able to handle pitching at Wrigley Field. He doesn’t just rely on one thing/pitch to get guys out.

Hoyer talks about the catching situation and what they have in Miguel Montero. He’s a great pitch-framer, great defensive catcher and a guy who really relates well to pitchers. Many people have told Hoyer David Ross is one of the best teammates in the game and an excellent clubhouse leader. These are the kinds of guys who can be mentors to a young team. They still like Welington Castillo a great deal, but Ross was just too good to pass up.

They knew they needed to add leadership this offseason to help build a winning culture. They feel really good about what they’ve added. Coaches can’t do everything. You also need teammates who can pull guys aside and correct bad behaviors or help guys who are struggling.

Young players are mainly thinking about staying in the big leagues/survival. There’s a necessary selfishness there, Bush says. We need guys who can help foster a team concept and make those guys more comfortable. That’s why they liked hearing Rizzo’a comments about wining the NL Central.

Next comes the question-and-answer session with fans:

  • The first question is about the draft and how they choose players. Epstein talks about how the track record for the best college bat is usually very good. They have a predisposition to that type of player with high picks. They tend to return about twice as much value as a pitcher at the top of the draft. You get your pitching through volume. You have to hammer it throughout the course of the draft.
  • How do you determine how young guys get at-bats? Javy Baez got a lot even though he struck out. Olt and Lake had a shorter leash. Hoyer said they wanted Javy to learn through his at-bats. They felt he needed that to get his feet under him in the major leagues. They wanted to bring him up and let him play. Lake and Olt lost time because other guys, like Chris Coghlan and Luis Valbuena, had strong seasons.
  • Here’s a question about when Kris Bryant is going to come up, especially if he hits in Spring Training. Epstein says it’s a balance of factors. It’s not just protecting the service clock. He uses Baez and Soler as an example. They’re trying to do the right thing for Bryant’s development and for the team.
  • The next question is about where the offensive production is going to come from. Epstein says there’s a good chance for improved production behind the plate with Montero/Ross/Castillo. But if the Cubs are going to be really good, it’s because young players are going to take big steps forward. They still really like Luis Valbuena at third, and Bryant will likely be up this year. But guys like Baez and Soler will have to step up. Alcantara can beat you with power and speed. There’s a lot of young talent on this team, but they need to take steps forward.
  • There’s a question about the development of the minor league pitchers like C.J. Edwards and Carson Sands. Rehman says Duane Underwood took some real steps forward last year. Jen-Ho Tseng has a four-pitch mix and throws up to 95. Really just a teenager. Edwards and Hendricks are more known commodities. Pitchers tend to surprise you more than hitters.

That’s it. Maddon and his Staff are next on the schedule. Stay tuned for more. We’ll be blogging all day today and tomorrow.

Cubs officially sign LHP Jon Lester to a six-year contract


(Photo by David Banks/Getty Images)

The biggest move of baseball’s offseason became official Monday when the Cubs and pitcher Jon Lester agreed to terms on a six-year contract that includes a vesting option for the 2021 season.

Lester, 30, is a three-time All-Star and a two-time World Series champion during his nine seasons with the Boston Red Sox (2006-14) and Oakland Athletics (2014). He has a pair of top five Cy Young Award finishes (2010 and 2014, both fourth), four top 10 finishes for the ERA title and six top 10 finishes in wins. The left-hander has made more than 30 starts in each of the last seven seasons, eclipsed 200 innings in six of the past seven and has three seasons with more than 200 strikeouts. His .634 career winning percentage (116-67) ranks fifth among all active pitchers.

The Cubs beat out teams like Boston, the Dodgers and San Francisco, who were all reported to have offered the southpaw significant deals. In the end though, the steps the Cubs had taken to produce sustained success swayed the starter.

“I believe in the plan and the thing that’s in place right now for the future of the Cubs,” Lester said. “Obviously leaving a place that you’ve already won and the comfort of that it’s difficult, but also you can relish in the process of enjoying the chance of winning a World Series for a franchise that never has just adds that little extra for me.”

Overall, Lester is 116-67 with a 3.58 ERA (635 ER/1,596.0 IP) in 253 major league appearances, all but one as a starting pitcher. Among big league left-handed pitchers active at the end of the 2014 campaign, he ranks best with an average of only 0.82 home runs per nine innings, second with 8.22 strikeouts per nine innings, third in ERA, fourth in wins and WHIP (1.28), and fifth with 1,457 strikeouts and 156 quality starts. He threw the 18th no-hitter in Red Sox history on May 19, 2008, a 7-0 victory against the Kansas City Royals at Fenway Park.

A World Champion with the Red Sox in 2007 and 2013, Lester is 6-4 with a 2.57 ERA in 14 postseason appearances, 12 as a starter. He has won all three of his World Series starts, posting a 0.43 ERA, and was the winning pitcher in the clinching Game 4 in 2007 in Colorado.

Lester turned in one of the best seasons of his career in 2014 when he went 16-11 with a 2.46 ERA in 32 starts with the Red Sox and Athletics. He earned an All-Star nod and recorded his lowest single-season ERA, which ranked fourth in the American League. He struck out 220 batters and walked only 48, good for a 4.6 strikeout-to-walk ratio that ranked seventh in the league. Lester was 10-7 with a 2.52 ERA in 21 starts for the Red Sox before being traded to Oakland on July 31, where he went 6-4 with an even better 2.35 ERA in 11 starts.

Eptsein and current Cubs General Manager Jed Hoyer were members of Boston’s front office for the majority of Lester’s tenure, with Epstein serving as general manager from 2003-11. Along with Lester’s success on the field, Epstein said he respects the pitcher’s drive and character, which were equally important attributes that led to the signing.

“He’s focused, competitive, hard working, intense and now fully mature. I think he’s got good self-awareness and understands the group concept,” said Cubs President of Baseball Operations Theo Epstein. “And he’s at his best in the most important moments, I think because he’s so driven and focused and not swayed on outside variables like pressure.”

The 6-foot-4, 240-pound Lester was originally selected by the Red Sox in the second round of the 2002 Draft (57th overall) out of high school and was in the big leagues just four years later at the age of 22. He made his debut on June 10, 2006, and made 15 starts before being diagnosed with anaplastic large cell lymphoma in late-August. Lester was declared cancer-free in December of that year and returned to the big leagues on July 23, 2007, going a perfect 4-0 with a 4.57 ERA in 12 outings (11 starts) down the stretch to help the Red Sox to the playoffs and a World Series championship.

Lester began his run of seven straight seasons with more than 30 starts in 2008 and has posted 15 or more victories in six of those seasons, including a career-high 19 wins in 2010, his first of two-straight All-Star seasons. He struck out 225 batters in consecutive seasons in 2009 and 2010, his single-season career bests.  In 2013, Lester went 4-1 with a 1.56 ERA in five postseason starts to lead the Red Sox to the 2013 World Series championship.

Now Playing: Joe Maddon makes his Cubs debut

It took all of about three minutes for Chicago sports fans to fall in love with new Cubs manager Joe Maddon. In his introductory press conference at the Cubby Bear, the spry and entertaining 60-year-old opened with a quick story about meeting Theo Epstein and Jed Hoyer in his beloved RV (the Cousin Eddie) and closed by offering to buy the entire press conference a drink. On Monday, Maddon became the 54th manager in franchise history, when he agreed to terms on a five-year contract through the 2019 season.

A two-time AL Manager of the Year during his nine seasons with Tampa Bay (2006-14), Maddon joins the Cubs after guiding the Rays to four postseason appearances (2008, 2010-11, 2013), including the organization’s lone World Series appearance in 2008 when he earned his first Manager of the Year award. He earned the honor again in 2011.

Here’s a quick look at some of the highlights from Monday’s press conference.